ethyl (2S)-2-methyl-2,3-dihydrobenzofuran-2-carboxylate | 1433062-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: ethyl (2S)-2-methyl-2,3-dihydrobenzofuran-2-carboxylate
• 英文别名: ethyl (2S)-2-methyl-3H-1-benzofuran-2-carboxylate
• CAS: 1433062-59-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: MLXMBPDRHXUERI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-methyl-2,3-dihydrobenzofuran-2-carboxylate 在 吡啶 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 (S)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis

  摘要：

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.

  DOI：

  10.1021/ja4018122
• 作为产物：
  描述：

  2-hydroxy-3-(trimethylsilyl)benzaldehyde 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二甲酸二异丙酯 、 sodium hexamethyldisilazane 、 氟化氢吡啶 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 ethyl (2S)-2-methyl-2,3-dihydrobenzofuran-2-carboxylate
  参考文献：
  名称：

  Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis

  摘要：

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.

  DOI：

  10.1021/ja4018122

文献信息

• Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis
  作者：Tomoyuki Yoshimura、Keisuke Tomohara、Takeo Kawabata

  DOI：10.1021/ja4018122

  日期：2013.5.15

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.